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Chemical Structure| 194473-09-1 Chemical Structure| 194473-09-1

Structure of 194473-09-1

Chemical Structure| 194473-09-1
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Product Details of [ 194473-09-1 ]

CAS No. :194473-09-1
Formula : C10H10N2O
M.W : 174.20
SMILES Code : O=C1N=C(C)NC2=C1C=CC(C)=C2

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Application In Synthesis of [ 194473-09-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 194473-09-1 ]

[ 194473-09-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 39549-79-6 ]
  • [ 108-24-7 ]
  • [ 194473-09-1 ]
  • 2
  • [ 39549-79-6 ]
  • [ 123-54-6 ]
  • [ 194473-09-1 ]
YieldReaction ConditionsOperation in experiment
85% With ytterbium(III) triflate; In 1,3,5-trimethyl-benzene; at 60℃; for 24h;Inert atmosphere; General procedure: 2-aminobenzamide (1, 1.0 mmol), 1,3-diketone (2, 1.5 mmol), Yb(OTf)3 (0.050 mmol, 5.0 molpercent),and mesitylene (2.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 60°C (bath temp.) for 24 h with stirring. The reaction mixture was then cooled to room temperature and analyzed by GLCand GC-MS. The product 3 was isolated by medium-pressure column chromatography on silica gel(eluent: EtOAc/hexane = 30/70 ~ EtOAc 100percent. For 3j, eluent: MeOH/CHCl3 = 30/70 ~ 50/50) andrecrystallization from MeOH/hexane. The products 3l and 3m were isolated by recrystallizationfrom EtOAc/hexane. 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6 (For 3j, in a mixture of DMSO-d6 and methanol-d4). Elemental analyses were performed at the Microanalytical Center of Kyoto University. The analytical and spectral data of 3a,10 3b-c,11 3d,12 3e,13 3f,14 3g-h,10 and 3j-l,7 are fully consistent with those reported previously. The products 3i,15 and 3m16 were characterized below.
  • 3
  • [ 64-17-5 ]
  • [ 39549-79-6 ]
  • [ 194473-09-1 ]
  • 4
  • [ 39549-79-6 ]
  • [ 78-39-7 ]
  • [ 194473-09-1 ]
YieldReaction ConditionsOperation in experiment
90% With acetic acid; In ethanol; at 110℃; for 24h;Inert atmosphere; Sealed tube; General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2?3 equiv) and absolute ethanol (2?3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12?72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:2,7-Dimethylquinazolin-4(3H)-one (8a). This compound was prepared from<strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (100 mg, 0.67 mmol), triethyl orthoacetate (217 mg, 245 L, 1.34 mmol)and acetic acid (121 mg, 115 L, 2.01 mmol) in absolute ethanol (2 mL) at 110 °C for 24 h to give105 mg (90percent) as a white solid, m.p. 260?262 °C (lit [49] m.p. 263?264 °C); IR (CHCl3): 3169, 1677 cm-1;1H-NMR (400 MHz, CDCl3): delta 11.6 (br s, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.47 (br s, 1H), 7.29 (dd, J =8.1, 1.0 Hz, 1H), 2.57 (s, 3H), 2.51 (s, 3H); 13C-NMR (101 MHz, CDCl3): delta 163.9, 153.2, 149.5, 146.0,128.0, 126.8, 126.1, 117.9, 22.1, 22.0; HRMS (ESI): m/z for C10H10N2O [M + 1]+: calcd.: 175.0871; found:175.0867.
 

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